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4-Aminopyridine → HCID 9820865, compound

HRID 1698801
Notes
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Reaction equation

HRID 1698801 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>CCOCC.C1COCC1>[N:28]1[CH:29]=[CH:30][C:25]([NH:24][C:18](=[O:22])[C:19]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=3)[CH:8]=2)=[O:20])=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 9671271-(4-Fluorobenzyl)-1H-indole

Product 1

HCID 9820865HCID 9820865, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4.75 g (21.1 mmol) of 1-(4-fluorobenzyl)indole in 25 ml of ether is added dropwise at 0° C. and under N2 to a solution of 2.25 ml of oxalyl chloride in 25 ml of ether. The mixture is refluxed for 2 hours and the solvent is then evaporated. 50 ml of tetrahydrofuran were then added to the residue, and the solution is cooled to −5° C. and treated dropwise with a solution of 4.66 g (49.5 mmol) of 4-aminopyridine in 200 ml of THF. The mixture is refluxed for 3 hours and allowed to stand at room temperature overnight. The 4-aminopyridine hydrochloride is filtered off with suction, the precipitate is washed with THF, the filtrate is concentrated in vacuo and the residue is recrystallized from ethyl acetate.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. customthe solvent is then evaporated
  3. addition50 ml of tetrahydrofuran were then added to the residue
  4. temperatureThe mixture is refluxed for 3 hours
  5. filtrationThe 4-aminopyridine hydrochloride is filtered off with suction
  6. washthe precipitate is washed with THF
  7. concentrationthe filtrate is concentrated in vacuo
  8. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9514695aee954e0b9f573e668cb53801
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344467B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes